A noncompetitive inhibitor of EAAT1
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UCPH-101

Item No. 21460

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-5,6,7,8-tetrahydro-4-(4-methoxyphenyl)-7-(1-naphthalenyl)-5-oxo-4H-1-benzopyran-3-carbonitrile
CAS Number
1118460-77-7
Molecular Formula
C27H22N2O3
Formula Weight
422.5
Purity
≥98% (mixture of isomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2)(1:3): 0.25 mg/mlDMSO: 25 mg/ml
λmax
225, 282 nm
SMILES
COC(C=C1)=CC=C1C2C(C#N)=C(N)OC3=C2C(C[C@@H](C4=C(C=CC=C5)C5=CC=C4)C3)=O
InChi Code
InChI=1S/C27H22N2O3/c1-31-19-11-9-17(10-12-19)25-22(15-28)27(29)32-24-14-18(13-23(30)26(24)25)21-8-4-6-16-5-2-3-7-20(16)21/h2-12,18,25H,13-14,29H2,1H3/t18-,25?/m1/s1
InChi Key
YBMGNDPBARCLFT-YDONVPIESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $69

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    1 mg

    $127

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    5 mg

    $525

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    Product Description

    UCPH-101 is a noncompetitive inhibitor of excitatory amino acid transporter 1 (EAAT1), which takes up extracellular glutamate in the central nervous system.1,2 UCPH-1 is selective for EAAT1 over EAAT2 and EAAT3 with IC50 values of 0.66, >300, and >300 µM, respectively, in a radioligand uptake assay using HEK293 cells transfected with the human transporter.3 It selectively inhibits anion currents in tsA201 cells expressing human EAAT1 (Kd = 0.34 µM) over rat EAAT4 and mouse EAAT5 at concentrations up to 10 µM.2 UCPH-101 is orally bioavailable in rats at a dose of 10 mg/kg but does not cross the blood-brain barrier.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Erichsen, M.N., Huynh, T.H.V., Abrahamsen, B., et al. Structure-activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-Amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101). J. Med. Chem. 53(19), 7180-7191 (2010).

    2. Abrahamsen, B., Schneider, N., Erichsen, M.N., et al. Allosteric modulation of an excitatory amino acid transporter: The subtype-selective inhibitor UCPH-101 exerts sustained inhibition of EAAT1 through an intramonomeric site in the trimerization domain. J. Neurosci. 33(3), 1068-1087 (2013).

    3. Jensen, A.A., Erichsen, M.N., Nielsen, C.W., et al. Discovery of the first selective inhibitor of excitatory amino acid transporter subtype 1. J. Med. Chem. 52(4), 912-915 (2009).